Tetrahedron
Tetrahedron
4 years ago

Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides1

Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides1
A highly enantioselective synthesis of chiral β-hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting chiral β-hydroxy thioesters were obtained in high yields (up to 82%) with good to excellent enantioselectivities (up to 94% ee). The synthetic application of the methodology is illustrated by the asymmetric synthesis of the selective serotonin reuptake inhibitor dapoxetine.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017305677

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